Bass Aackwards: Dating Style.

August 5, 2012 2:28 PM

If I had only known how awesome you are I would have never moved in with you...

So. I am a 28 y/o woman who, six months ago, moved into a small, two bed/one bath with a friend. We had hung out a bit casually beforehand (always with other people) and have a bunch of mutual friends. We both play music and I have played a few gigs with him, guesting with his old band. Then, suddenly come January, both of us were looking for somewhere to move at the same time, so we decided to go in on renting a house together.

Six months later and he has become my best friend. We hang out all. the. time. When we moved in I never suspected that I would develop feelings for him because I had never really hung out with him much beforehand. I thought it would just be a chill living situation because he and I had always gotten along and, from what I could tell, he was a nice, drama-free, calm guy. I thought we might see each other in passing, maybe share a meal at the table once in a while, but mainly keep to ourselves. Boy, was I wrong.

Over the past six months I have become very fond of him. He is smart, funny, patient, kind, generous, caring, interesting, respectful, mature and we very nearly share ALL the same interests. (Music, RPGs, tabletop RPGs, comics, movies, food, hang-outs etc. etc.) We go out and do things together frequently (see movies, get drinks, have dinner) and stay in and do things together frequently (play video games, cook together, play music, watch movies, etc.) Effectively, this is what I would want out of my ideal relationship. When we go out together, even though we are not flirty or touchy with each other and act strictly as friends do, people often assume that we are in a relationship... and seem pleased about it.

I only mention last that I am very attracted to him because I don't want anyone to think this is merely lust or infatuation. I have never once touched or flirted with him (honestly) out of respect for the circumstances and so as not to make him uncomfortable... but boy, do I want to. It has been getting increasingly more and more difficult for me to fight the urge to just reach out and pull him close when we are just hanging out watching movies/doing whatever.

I know this has the potential to be a disaster but I (perhaps foolishly) am prone to being optimistic. I want to tell him my feelings, which are that I have been looking for someone like him for a long time... I just had NO idea that this person was going to be in arms reach... as my room mate. I also am not under any illusions that he feels a certain way or not, or is obligated to, due to our time spent together. I have been hanging out with him as a friend and that's all it is, and all I ever expected out of it. If he doesn't feel the same way, I might be a little disappointed, but I haven't been taking his actions to mean more than what they are at face value.

So I pose these questions to you: Should I tell him? If so, how? And lastly, if the men of the hive-mind have insight into his behavior from what I've told you, do you think he might feel the same? A few months into living together he stopped bothering to go out and date girls/bring anyone home... he said he's "taking himself off the market until he gets his life straightened out" (meaning, financially/job-wise - we're both on some hard times financially right now but are making things work somehow - equally, mind you.) I have never had anyone spend the night because I honestly have no interest in meeting anyone else until I get these feelings sorted out.

Fun facts: I dislike drama, so I avoid it/do not cause it. I consider myself to be pretty mature about these things and have maintained friendships with most of my exes (both long term, serious ones are good friends and happily married/coupled)... I do not get jealous easily. I do think I would feel a little awkward if he brought a girl back here for the night, but I wouldn't say anything about it at this point - it's not my business.

Sorry this was long and thanks in advance! If anyone has questions, OP will deliver. :)

posted by bzzt to human relations (61 answers total)

How reliant are you on this living situation - do you have enough money on hand to move out/sublet if things went sour? Do you have other friends you could roommate with?

How much longer is your lease - could you wait a bit longer to bring this up until you're closer to ending or renewing it (as an easy endpoint in case it doesn't pan out)?

I think you sound pretty calm and rational about the whole thing (the way you've presented yourself here) so I would say if you have the above bases covered - and you're careful to bring this up to him gently, without him feeling he has to go for it or turn it down right away (so as little pressure as possible, and a lot of room to stay friends if he's not interested) - then I would go for it.

But I'd totally advise you do it in a casual, light-touch, and mostly sober way - not, say, one night when you're both quite drunk! When you've built it up to this point in your head it's pretty likely you're going to make a move soon when your inhibitions are down - and that has the potential to go just fine, even be exciting - but it also has a greater chance to be full of misunderstanding and regret.
posted by flex at 2:40 PM on August 5, 2012 [1 favorite]

1) What are you looking to get out of telling him?
2) Is he also interested in the path that you are interested in (as far as you know)?
3) What will you do if he is does not feel the same as you?
4) What will you do if this changes the dynamic of your friendship for the worse?

I am not asking rhetorically, a large part of the advice I would give is based on the answers to these questions.

Also: it's good that you dislike drama, but that doesn't mean that it can always be avoided just by virtue of your dislike. Your feelings may be heading towards the F5 drama tornado area. This situation might not be easy or drama free by virtue of the fact that you live with him as a roommate yet have feelings for him. Are you prepared to face the possible drama that may result from his feelings regarding the situation?
posted by Shouraku at 2:47 PM on August 5, 2012

This happened with some good friends of mine way back. He made the move not her. I was there that night while she went to her room to think about it and he paced the living room like an expectant father in the 50's.

They were together for 15 years.
posted by merocet at 2:54 PM on August 5, 2012 [7 favorites]

Life is short. Go for it.
posted by ZipRibbons at 2:57 PM on August 5, 2012 [37 favorites]

I would just ask him if he's receptive of the idea of going out on an actual date. Make a deal out of it. Say, you want to go some place fancy and or special (something that's not your normal nerdery). Then let him know you don't kiss on the first date. If he's receptive, great. If it goes well, great. If he's not interested I'm guessing he'll let you know prior to actually going out. If you go out and things are awkward maybe this isn't meant to be.

I wanted to be coy in my reply and say, "Repost this question in two weeks. I bet it'll have resolved itself by then." Seriously, we're hardwired to express some sort of interest in those we are attracted to. You'll eventually be unable to keep your feelings hidden.

I think this is a great way to form a relationship. You already have a solid foundation of shared interests and respect.

The worst that can go wrong is you're looking for a new place to live.
posted by cjorgensen at 2:59 PM on August 5, 2012 [1 favorite]

It is not clear that he feels the same, and unloading all these feelings in a gush would be awkward. But I don't see a problem with being clear about your contentment with your friendship while asking if he's ever thought the two of you might work as a couple.
posted by Monsieur Caution at 3:00 PM on August 5, 2012

Flex: First, thanks for the reply! Second, the lease ends in 4 months... and I suppose I would be able to move if things went bad. I have less belongings than most and a steady job so it would be a pain in the ass but yeah, doable. I've thought of leaving him a note that he can open when he goes away on a weekend trip to visit family in a few weeks, and then saying something that lets him off the hook in case he doesn't feel the same - like, he could come back and talk to me about it, but if he doesn't want to go there and doesn't bring it up when he gets back then I just won't mention it and things will continue on. (probably would spend a little less time together, though.) Eh?

Shouraku: Thanks for the reply! 1) I guess I am looking for a potentially awesome relationship... I suppose I'll never know if I don't bring it up somehow, right? 2) Well, from what a close (male) friend has said it seems like, from the way my room mate treats me, it is unusually nicely for someone who has no feelings. Then again, I did say my roomie is a nice guy in general (hence, the confusion) 3) If he doesn't feel the same I will probably spend less time one-on-one with him and renew my efforts on the dating front elsewhere, and hopefully remain good friends. 4) I can't imagine it changing the dynamic for the worse, I kind of just want to "put it out there" and if he doesn't feel the same, no hard feelings. I've had my heart broken a couple times before and am FAR more realistic about how the world works now, and a little battle-hardened :P
posted by bzzt at 3:01 PM on August 5, 2012 [1 favorite]

I'm a man, and from what you said about him here I don't think me or anyone else would be able to guess what he's thinking one way or another. He may have no interest whatsoever, he may feel the same way you do and not be making any moves for the same reason, or maybe he has some feelings that are ready to develop if you poke at him a bit. Its all possible.

I'd say - go for it. You'll never be able to live with yourself if you never find out. Worst case scenario you move out and perhaps try to salvage a friendship. Worst case scenario kind of sucks, but I think doing nothing and torturing yourself is even worse.
posted by tempythethird at 3:01 PM on August 5, 2012 [7 favorites]

We need some more relevant information. You said he no longer goes out and pursues women but is he a naturally shy person or is he outgoing when confronted with women he's interested in? If it's the former, I'd say go for it. If it's the latter, I'd say he would have probably made a move by now if he was remotely interested in you.
posted by MaryDellamorte at 3:02 PM on August 5, 2012

I've thought of leaving him a note that he can open when he goes away on a weekend trip to visit family in a few weeks

Please don't do this. On the chance that he doesn't feel the same way, it could ruin his entire weekend.
posted by MaryDellamorte at 3:04 PM on August 5, 2012 [6 favorites]

Given your update, he is what I would do:

"Kind and Sexy Roommate, I just wanted to let you know that I would like to go on a date with you sometime if you would like. If not, that's fine too as I also value our friendship just how it is."

You seem to be very mature and level headed, and your update indicates that you seem to be okay with whatever answer he may give, so I say go for it. Good luck to you!
posted by Shouraku at 3:06 PM on August 5, 2012 [5 favorites]

I definitely think you should go for it, knowing that there is a possibility that it could go disastrously wrong to the point that one of you would move out and the friendship ends. I doubt that -- I suspect it'll either be relief and mutual attraction, or mild discomfort and you both deal with it like grownups. I mean, what if you weren't attracted to him, and your perfectly nice but totally unsexy flatmate expressed his attraction? You would probably feel a bit sorry for him, things would be a bit awkward while he processed your rejection, and you'd stay friends, if perhaps, as you say, hanging out a bit less.
posted by Forktine at 3:08 PM on August 5, 2012

Get a mutual friend to take him out for a beer. After a couple drinks, mutual friend asks "so, are you and roomie (OP) dating? Why not, you'd be awesome together, blah blah blah" and see what his reaction is.

I know it's a little high school, but I really feel you need to test the waters a bit before diving in to this pool.
posted by no regrets, coyote at 3:11 PM on August 5, 2012 [21 favorites]

MaryDellamorte - Yeah, you're right. Better not with the note. As for the first question, he's definitely not shy. That being said, from what I've seen (and heard), he is a very respectful person when it comes to "the ladies" - he was raised by his mom and has two sisters, who he loves, so he is actually pretty sensitive about romantic/social situations. We've had lots of conversations about our lives before and it seems like he doesn't like to jump into things, and is a patient guy. I can't help but wonder if he's just being *gasp* mature and cautious about it...?
posted by bzzt at 3:15 PM on August 5, 2012

I'd say it's likely the idea of being together has crossed his mind at some point, but the close friends living together situation is a powerful deterrent, and while he could have a secret crush like you, it's more likely that he's firmly in the friends headspace. Which means he'll be caught off-balance if you make a move and might kind of freak out a bit, until he has time to process it, and to start think about you in a different way, at which time things might change.

I think maybe the way forward is a very slight change in behavior -- for example, a lingering glance and shy smile when you say good night, looking over your shoulder as you walk into your bedroom. Very subtly flirtatious. Keep it up for a week and see how he responds. Then if you do feel the time's right to try something more overt, he'll be mentally ready for it.
posted by PercussivePaul at 3:24 PM on August 5, 2012 [1 favorite]

Aside from the usual "don't shit where you eat" provisions involving dating roommates and coworkers, I don't see any major obstacles to you giving this relationship a shot. At worst, you break up after a few months and have to deal with finding separate apartments, negotiating an end to your lease, et cetera. Or you ask him out, he rejects you, and you have a few awkward weeks as you navigate what this means for the friendship. If you're ready to accept those risks, I say go for it. You only live once.
posted by deathpanels at 3:25 PM on August 5, 2012

I know this is an AskMe cliché, but you expressed yourself really well in this question, and you could do a lot worse than just showing it to him! If it were about me I'd be either thrilled and charmed (if I were interested) or flattered and not terribly uncomfortable (if I were not).
posted by nicwolff at 3:33 PM on August 5, 2012 [1 favorite]

My best friend was in this situation exactly with her roommate. They lived together for over a year before they hooked up. That was eight years ago. They are lesbians and well-versed in the art of discussing feelings, and they communicated about every single pro and con--over and over, ad nauseam--before deciding to give it a shot.
posted by Lieber Frau at 3:35 PM on August 5, 2012 [1 favorite]

If he is as mature as you say/believe he is, then having a discussion about this should go well.

While fear of rejection is a rational fear, the worst case scenario of being rejected by this guy is that you move out. Which you have said would be doable though sucky.

Don't approach this with the phrase "we need to talk" or "hey, let's sit down here and have a chat." Sometime soon, when you are talking about a show one of you wants to go see, or a restaurant one wants to try, you look him briefly in the eye and say, "HEY...do you want a date for that? Because I'd like to try dating you." Do not use any code word like "get to know you better." Use the words date or dating. (But be careful of the word relationship. YMMV with regard to that.)

Then be quiet. Don't gush about how wonderful he is. Don't gush about anything. Don't admit that you're embarassed or sorry for making this awkward. Just be quiet. Give him a quiet minute to process and respond. If you keep talking it increases the pressure on him. If he agrees, set up a time when you'll be ready to go.

Last, if he makes any excuse for why dating you is not on his list of things to do, no matter how bullshit the excuse sounds!, Do Not Counter. Seriously. Do not point out that he will have more time when _x_ is complete, or that he's not a jerk, or that he's really awesome if he claims you deserve better. Just say, "hey, thanks for listening. I'm going to not make this awkward." And then let it drop, because he is not interested.
posted by bilabial at 3:47 PM on August 5, 2012 [25 favorites]

What are his feelings towards you? Has he ever hinted at anything?? A man who is interested in you will sooner or later make a move. He would not wait for 6 months.
posted by pakora1 at 3:54 PM on August 5, 2012 [1 favorite]

A man who is interested in you will sooner or later make a move. He would not wait for 6 months.

Actually. No.

Men are not a monolith. They just are not.
posted by bilabial at 4:04 PM on August 5, 2012 [29 favorites]

A man who is interested in you will sooner or later make a move. He would not wait for 6 months.

This is 100% false. I could be head over heals with a roommate for years and never say anything. The roommate bridge is a tough one to cross, as OP knows.

To be totally honest, if I were you I'd get the both of us drunk one night and see how cuddling up to watch a movie goes. If you make out or hold hands or something, the next day you can say "hey, I know we were drunk last night but I actually like you". And if it doesn't work you have plausible deniability thanks to the booze (thanks, booze). But that's me -- you should probably talk to him or something (blagh).
posted by no regrets, coyote at 4:04 PM on August 5, 2012 [14 favorites]

Wow, thank you everybody for your replies. It is awesome to get a sense of how a group sees things and get different perspectives - I really appreciate it!

Pakora1 - There have been some hints, but I don't want to be the stereotype that turns something that could be a hint into something that definitely means he's into me just because that's what I want it to mean. I'm kind of a science-type in the sense that I like cold, hard, facts - haha :) And he is definitely a unique guy when it comes to gender-stereotypes - Like I said, I've been looking for someone like him for a long time - he really seems to see women as people and respect them a great deal, and definitely likes to do things the right way - as well as think things through before taking action. These are qualities I value highly...

I am still mulling over the exact course of action, but I think that I will "go for it" in one way or another... I know that my last thought, if I were to get hit by a bus tomorrow, would be "Man, I really wish I had asked my room mate out." :P
posted by bzzt at 4:15 PM on August 5, 2012

I know some folks who were in this same situation. They got together due to a drunken cuddle time almost exactly like no regrets coyote describes. They're engaged now.
posted by phunniemee at 4:16 PM on August 5, 2012

Imagining myself in his shoes, I'd much prefer something pretty direct and easy to turn down--or say yes to--like what Shouraku suggested, rather than the subtle flirtation angle. I think I'd find the subtle flirtation from a roommate awkward, ambiguous, and impossible to really answer directly. Also I could certainly see myself not making a move in his situation.

Sounds like others might feel differently.
posted by spbmp at 4:16 PM on August 5, 2012 [2 favorites]

I really like the paragraph in your question that starts with "I know this has the potential to be a disaster but..." and ends with "...face value." It says everything there is to say in a non-drama-y, non-expectant way. I vote that you say exactly that to him and go from there.
posted by lunaazul at 4:50 PM on August 5, 2012

Don't get drunk an make a move! That makes it seem insincere or thoughtless. Put in a movie you've both seen before and love. Say, "hey listen. I think you're really great and would love to be more than just friends. If you feel the same way, let me know. If not, I'll speak nothing more of this."

If he says he likes you back and thr moment seems right, kiss the hell out of him! If he doesn't, continue normal movie jokes and hope the awkwardness doesn't ruin anything.
posted by two lights above the sea at 4:50 PM on August 5, 2012 [2 favorites]

I think you've got the recipe for success here: similar interests, you enjoy being together and you're attracted to him.

Try and let him know your feelings but give him as little pressure as possible.

I'm hoping for the best!
posted by Fister Roboto at 5:02 PM on August 5, 2012

Go for it. Don't do anything crazy like trying to make a move on him or spilling your guts to him in a great big outrushing -- you need this to be as low-drama as possible, and that's the best way to get what you want anyway. Your goal for the moment should be to get a date with him, not to fuck him or to make him understand that he's your One True Love.

Maintain some self-control and approach it as you would any other time that you had intentions on someone: just tell him that you think you're interested in maybe being more than just roommates and would he like to perhaps go out on a date with you and then maybe take it from there if it goes well? Let him know that you understand that it's not ideal given that you already are living together, but that you'd really like to take a shot at it anyway, if he's willing. Can't say for sure, but I bet he'll take you up on it.

Try to phrase this in such a way that it's obvious what your intentions are but that still allows both of you room to back away with a minimum of awkwardness should that be necessary.

If you play it right there's no reason why it should explode your entire living situation right then. There might be some extra awkwardness if he's not interested, but things are pretty awkward already it sounds like. It may be that you guys will become a couple but it won't work and then, yeah, you'll probably have to move out -- but the least is up in four months which means that you'll be able to get out in not-too-long if you have to. That's not ideal, but then on the other hand if things are fortunate enough to go superbly then you'll already be there, living with him. That happens sometimes! Not that you should count on it, but it wouldn't be the first time.

I don't think that the fact that you guys live together should be a dealbreaker. You should approach the situation with a little extra caution and you should steel yourself to move out at the end of the lease if things go really badly, but I think as long as you don't do anything nuts then you should go forward.
posted by Scientist at 5:08 PM on August 5, 2012 [1 favorite]

I'm a guy and one of my Absolutely Unbreakable Rules (TM) is "Don't s--t where you eat." In other words, never date co-workers, clients, or roommates. In fact, I don't even date friends unless I'm explicitly told that it will start out as no strings attached, so that I know I'm not risking the friendship if things go south.

That said, I know that there are situations that I could be tempted to do so, and it sounds like this would be one of them. You just need some Drunken Cuddle Time (TM). The purpose of the alcohol is 10% to loosen inhibitions, but 90% to give both of you plausible deniability - so that if you make a move and the other person reacts poorly, you can say the following day "God, I was soooo drunk last night. I apologize for that outlandish behavior. You know me pretty well by now and you know I'd never do something like that sober, right?"

The important thing is that you don't want to actually get that drunk, since throwing up is a moodkiller. You want to drink just enough that you have a plausible excuse.

Another idea I would like to float by (which could be an excellent prelude to Drunken Cuddle Time) is to go out dancing with him. If the two of you are drinking at a club, start dancing together, and you grind with each other a little (as seems customary among the young kids nowadays) it'll be pretty easy for you to tell whether he likes you or whether he REALLY likes you. That's the thing about external reproductive organs - from an anatomical perspective, they give very good "hints" about what a man might be thinking about.

So, I'm thinking maybe the following sequence might work: 1) go to a club together 2) drink and dance at the club, 3) go home together and cuddle on the couch, then 4) kiss the boy.
posted by wolfdreams01 at 5:11 PM on August 5, 2012 [3 favorites]

I know a couple that got together this way too..not only were they roommates but bandmates too. They drunkenly hooked up, and actually the first year or so was a drama mess because neither of them wanted to settle down. They tried to 'just be friends' but the hook-ups and emotional to-and-fro kept happening.
Its 4 years later and they just got married.
Let us know how it works out for you!
posted by hellameangirl at 5:26 PM on August 5, 2012

I'd just ask, very matter of factly, "We get along so well, do you think we should try dating?"

That's it. No drama, no big declarations of love. He can say, "You're right, we do have a great time together, why not?" Or he could say, "I'd worry about screwing up our roommate and friendship thing." Be respectful of whichever way he answers.
posted by Ruthless Bunny at 5:32 PM on August 5, 2012 [19 favorites]

I like Ruthless Bunny's approach. Something like, "we get along so well, do you think we should try dating? Take [X movie] for instance. Would you like to go on a date with me to see it?"

You could also try cuddling up on the couch. But asking him on a date has the benefit of announcing what's going on, so that it's not all "what just happened?" awkward. You go on one date, and then if all goes well, future couch cuddling will be mutually understood.
posted by salvia at 5:57 PM on August 5, 2012 [1 favorite]

The traditional way to deal with this is to have a few drinks and/or smoke some weed, then cuddle up to him and put your mouth where he can kiss it, or kiss his cheek, or hold his hand, or whatever seems nice to you. Then if he reacts badly you can blame it on the alcohol/weed and both forget about it.
posted by the young rope-rider at 6:00 PM on August 5, 2012 [4 favorites]

My husband and I were friends for about 4 years before starting dating. I'm not sure which of us realized that we liked each other *that* way first, but he made the first move. We went out to dinner on Valentines day (which he thought was a date and I thought was just our normal going out like friends) and after that he told me how he felt and the rest was history. We've now been married 6 years. Just tell him how you feel, but be accepting if he doesn't feel the same way. Good luck!
posted by katers890 at 6:56 PM on August 5, 2012

Aa a guy, it's hard to say. He could be into you or be really happy with the quasi relationship y'all have now while he gets his shit together.

You know him better than us. Would a "pull him closer to cuddle" move work better than a talk? Only you know know, so choose one of those and definitely go for it. Sounds too good to at least not try.
posted by Brandon Blatcher at 7:28 PM on August 5, 2012

One thing to think about is how his previous breakups have been, as they can be a good indicator of how maturely he might handle this. Does he talk badly about his exes? Were they all "batshit crazy" or is he still friends with them?

Go for it, but 1. make it as easy as possible to de-escalate and slide back into friend mode and 2. have a real backup plan if shit does go way south.

Also, nthing the opinion above that men will not necessarily make a move if they are interested.
posted by ropeladder at 7:39 PM on August 5, 2012

I married my roommate.

We hooked up about a week before we moved in together, and things were going that way, anyway, but YES! This can and does work out.

Now, I eventually divorced that guy, and I am happily married now to someone else, but in the meantime...

There was my very best friend. I met him when we were living in the same apartment building. Anywho, we became close, he was hugely respectful towards me and very lovely (which is how I started developing feelings for him over 2+ years...) Finally one Christmas, I just sprang it on him after returning home from a party together - Hey! I like you!!

He did not feel the same way. And he was so nice about telling me directly, it hardly hurt a bit.

Our very close friendship carries on to this day! We're still GREAT friends!! He has a girlfriend who is like family to me. My husband of 4 years is beloved by them!

In short. You can not lose when shit is solid. This will be awesome no matter what. Pick your moment and tell him!


The worst thing that happens is you immediately get rid of that "attraction feeling" (it'll naturally disipate - trust me) because you'll find out he doesn't feel same.


If the friendship is solid, this will be a boon or a blip, but it won't be dramaz.

Go for it. Be honest.

You rock for being true to your feelings, either way.
posted by jbenben at 7:45 PM on August 5, 2012 [4 favorites]

You seem like a lovely person. I like everything you've said about this, I like your attitude about it, and for that reason, I think you're okay to pursue it a bit and see what happens, because I think you can handle it if it doesn't go the way you hope.

The most important thing, I think, is to make sure that the friendship is safe -- because it's so special to you -- no matter what happens. You can't prevent it from being awkward if he doesn't feel the same way, but I feel like the more straightforward and low-key you can be (and you seem like the rare person who perhaps can be), the happier you'll be. I think a bunch of these approaches could work. I'm not crazy about the drinking gambit, just because it won't be clear after the fact whether it "counted" or not, you know? I find myself surprisingly drawn to the option of having a friend run it up the flagpole with him for you, which might not tell you much -- if he says, "Oh, I don't know, it's not like that," you won't really know whether he's just keeping his cards close to the vest -- but if you have the right friend with a REALLY delicate touch, it might work.

If you can safeguard the friendship either way, then you truly have nothing to lose, which is why that's what I would make your priority. Good luck to you.
posted by Linda_Holmes at 8:02 PM on August 5, 2012

Oh if the drinking thing goes well, you stay up talking about how much you like each other. You don't really get that drunk anyway, it's mostly just a face-saving excuse.
posted by the young rope-rider at 8:23 PM on August 5, 2012 [1 favorite]

I hooked up with my roommate, and we've been dating 6 years and counting. Such a big fan of taking the plunge, especially in a situation like yours. You sound like a kind and intelligent person, as does your guy friend. Considering that you've both been doing such a good job being respectful of boundaries for six months yet have coincidentally both made the other the focus of your respective social lives (it sounds like), seems like any move you make would be happily received! You'll figure out how best to do it (quietly crossing the physical boundary was always my M.O.) and I bet it will go great. Good luck!
posted by dahliachewswell at 9:35 PM on August 5, 2012

If the friendship is solid, this will be a boon or a blip, but it won't be dramaz.

Go for it. Be honest.

this is true, right here ^^

for what it's worth, my (now) husband and I were not roommates, but were very close friends and teammates on the same cycling team, prior to getting together and actually dating. But the potential fallout was similar; my teammates are a very small fishbowl and very close knit and I really did not want to screw up a good friendship or create unnecessary drama within the team (because that shit is just wrong).

In his case, it was a late night, a convenient snowstorm that stranded him at my place, and his portable hard drive full of Top Gear episodes that he seduced me with gave us both the intimate cuddle space and subsequent courage to really express "hey, you know, I really LIKE, like you..."

And the thing is, in retrospect, we are both mature enough that if nothing or even just a fling had come from that snowy night of lowered inhibitions? We both would have been just fine with it.

Talk to him. I wouldn't be surprised if there's some reciprocation there. And what's the worst that could happen? He doesn't feel the same, no harm, no foul, you've cleared the air, and you're free to put all this pent-up energy into something or someone else. I think if you guys are as solid as you say, then you should be okay no matter what.
posted by lonefrontranger at 9:48 PM on August 5, 2012 [1 favorite]

After a two year friendship, my now girlfriend said 'I think I might have a bit of a crush on you'. We've been together for nearly five years now.
posted by knapah at 3:07 AM on August 6, 2012

I agree that you should go for it, but I'd like to slightly adjust your plans. Don't tell him how you feel, ask him out. Asking a question that he can say yes or no to makes it easy to respond. Telling him how you feel and then saying, "so what do you think?" puts a lot of pressure on him. He didn't expect to be in a conversation where he gives a full accounting for his feelings, and now suddenly he is, and that might make him uncomfortable. So, a couple of drinks, followed by a "do you ever want to go out as more than friends?" is the way to go.
posted by Ragged Richard at 6:46 AM on August 6, 2012

Hey, everyone - thanks so much for all the wonderful advice - I really feel a lot more confident about navigating this situation now!

I wish I could mark more than one "best answer" because what I think I'm going to do is a combination of a few. I really liked Ruthless Bunny's answer - very direct, a yes or no question, something easy to say and answer. Sometimes the simplest course of action is the best one, right?

So I think at some point this week I'm going to feel out the waters and when the right moment presents itself, go for it. I'm not gonna express my feelings, 'cause that might make him feel backed into a corner, but I'll just keep it short and sweet.

Neither of us go clubbing or dancing, but we did stay up until 2am to watch the Curiosity rover land on Mars, if that gives you guys a better feeling of our personalities... We have been drunk around each other a lot actually so it would be weird at this point if all of a sudden I was like "Ohmygosh I don't know what I'm doing" *snuggle* because I can hold my liquor pretty damn well haha - but maybe a drink or two would work to help the inevitable nerves.

Anyway, I'll let you guys know how it goes when it happens!
posted by bzzt at 7:01 AM on August 6, 2012 [1 favorite]

We have been drunk around each other a lot actually so it would be weird at this point if all of a sudden I was like "Ohmygosh I don't know what I'm doing" *snuggle* because I can hold my liquor pretty damn well

To be clear, both you and he would probably have a good idea that it was not "just the liquor", but it would give you a nice little binkie to hold on to so that you could move forward without it being totally awkward.
posted by benbenson at 7:05 AM on August 6, 2012 [3 favorites]

Yeah, don't worry too much about making it perfectly non-awkward or 100% possible to transition perfectly out of and "never speak of again." Life is messy. I dunno -- try the Tao way. You know you like him. So just be like that. "Show, don't tell." Don't you think there will come a moment when you can say everything by just smiling, or touching his hand? Maybe it will turn out a bit awkward, but how bad could it be? Your description of things definitely doesn't make me think that you will "ruin your friendship" or anything crazy like that. Neither of you sound likely to freak out. You're people who live together and like each other, of course love is something that you both at least think about. It sounds like there's a lot of warmth in your relationship and it's just about kinda trying to spark it and see if it burns. If not, it's all good. Best wishes!
posted by mbrock at 8:17 AM on August 6, 2012

Go on an Kiss da girl.


Seriously. Telling someone you like them, even if they like you back can turn a romantic moment into a discussion. In my experience that is not good. I've had long term very close friends tell me they liked/loved me, (and I liked them back) we talked about it a bit and then sat there/went to bed/left etc. I was 0/3 until my wife and I just kissed, shattering our long term friendship.

Making a choice is hard because it is a destructive act. You are say yes to one thing and no to another. If you really want him to be your lever you will have to risk him not being your friend. Trying to have both is going to diminish your chances for either.

You must decide. Then kiss him.
posted by French Fry at 8:31 AM on August 6, 2012 [1 favorite]

Eye contact, compliments, smiling, light touching, same as always.

Flirting is about respecting boundaries by taking very small steps. I'd start with the eye contact. When you are talking to him, maintain eye contact longer than normal. Obviously not insane staring, but you'll get the hang of it quick.

Smile a lot at him. I bet you might do this already. And next time he looks good, tell him. Eventually, the hand on the back, hand on hand--you'll get the hang of it as you move foreard.
posted by Ironmouth at 9:57 AM on August 6, 2012 [1 favorite]

I think I'm off the bell curve on this one, judging by the above answers, but were I in your roommate's shoes, I would much prefer to be approached about this verbally than for you to make a subtle flirtatious physical moves like cuddling or going in for the kiss. The empirical experience that I bring to the table for this question is having about six of my best guy friends develop feelings for me and ask me out in a variety of ways - some verbal, some written, some attempted drunken kisses, some attempted cuddling, etc. These weren't roommate situations, but they involved similar dynamics of a guy/girl friendship when one party wants more but doesn't want to ruin the friendship by trying.

While alcohol and making a physical move may seem like the best option, as it offers plausible deniability the next morning, I find this the absolute worst option. First of all, it leaves it unclear to him the extent to which your actions were motivated by the booze, and it doesn't do justice to your long-thought-through feelings about him. I also personally find it very difficult to clearly turn down ambiguous physical moves that may or may not indicate romantic interest, as it feels presumptuous to assume that they necessarily do (arm around me, lingering hug, etc.). I feel a deer-in-the-headlights moment of awkwardness, frantically think about how best to clarify, and end up missing the moment in a torrent of awkward, and the guy is left confused about whether or not I reciprocate his feelings, and the awkward and confusing mess is prolonged. I then do my best to avoid the person in question, to avoid a potential repeat. YMMV.

My recommendation would be a simple, explicit, and drama-free verbal approach, using the word "date", and making clear that you value your friendship and that it's not in jeopardy if he turns down your romantic advance. No elaborate and overwrought declarations of love, no alcohol, and no confusion about whether you're making a romantic move or simply expressing admiration for him as a friend. Clear, to-the-point, and drama-free, and if he's not interested it won't be agonizingly prolonged and he shouldn't feel reason to avoid you. That would be my strong suggestion. Anything other than an enthusiastic "yes" should be interpreted as a "no", in case he feels some pressure to be nice by equivocating rather than rejecting you; he can approach you if he changes his mind. Even if he turns you down (as I did with almost all of these guys), most people are flattered by the knowledge that someone that they admire and respect has romantic regard for them. Being so forthright and clear is, as far as I'm concerned, a gesture of kindness to a friend: you uncomfortably blur the boundaries of your friendship for as little time as possible, and you show a courageous willingness to own your feelings for that person without the cloak of alcohol or ambiguous gestures.
posted by UniversityNomad at 12:30 AM on August 7, 2012 [1 favorite]

Ask him.

(Data point: my now-fiancé and I started out as (randomly assigned) roommates who became good friends. I am gutless and did not say anything, but after a mutual friend spilled the beans, I kissed him and things worked out swimmingly! If he hadn't been into me, it would have been awkward for a while, and then we would've moved out and moved on. But the benefits definitely outweighed the risks. Also, re: the above, alcohol and making a physical move worked out for me. Again, gutless. YMMV.)
posted by goodbyewaffles at 5:29 AM on August 8, 2012

I keep checking back to this thread. Would love an update!
posted by bearette at 9:34 PM on August 8, 2012 [2 favorites]

Ah - update, I guess: Still haven't asked yet, we have kept hanging out though. Things for him have been stressful over the past few days (work/money/friends) and I'm waiting for a time when he is happy and relaxed. If there is one thing I've learned in my relationships so far it is that timing is very important! (More important that I used to think, at least!) I will respond here with news when this plan goes down, though.
posted by bzzt at 7:30 AM on August 9, 2012

Good luck! Let us know how it goes!
posted by no regrets, coyote at 1:59 PM on August 9, 2012

I'm so looking forward to hearing how this works out! I did something similiar a few years back - I told a long time best buddy that I'd always been curious about dating him. He was flattered, and surprised, and started saying reasons why it wouldn't work - and I just told him, I'm not asking you for anything, don't worry, I just wanted you to know, that's all.

I felt that was really key to keeping things cool - I just offerered him some additional information, but made it clear I had NO expectations.

We continued hanging out for the few days I was in town, and I sensed a slight difference in his actions that seemed to be in my favor, but then I went back home to another country and we stayed good friends like nothing had ever happened, and he's married now, so it's all good.

It did feel pretty good to tell him, and when you tell someone who really cares for you - they know how to take it and still be cool.
posted by Locochona at 5:23 AM on August 10, 2012

When I first read this, I was sitting with my former roommate, who I'm now dating, and we agreed that it was a sweet question and that we liked reading it and felt like we should have something to add, but really just didn't because our relationship was such a surprise to both of us, and was something that neither of us wanted while we lived together. It's not that we didn't think of it because, even though we were both usually happily dating other people, people we knew would ask why we weren't dating and strangers would assume we were. We joked that we should get shirts that said "we sleep in separate beds." But neither of us was secretly in love with the other, or even secretly in crush with the other, and it was many years (of continued close, platonic friendship) after we stopped living together before we ended up together.

I give all this background because it occurs to me that perhaps part of why it took so long is not just that we are special snowflakes and our love is unique, but because of something about the roommate relationship that made it totally unthinkable for us to be together while we lived together, and even in the years after that. Perhaps the "don't shit where you eat" mentality referenced above can be so internalized that it becomes akin to feeling like siblings (which we definitely did. and, uh, don't anymore.). And obviously this hasn't happened for you, but if it ends up being the case that you do ask him out and he's not interested, it might be helpful to consider the possibility that he may just have internalized a sense of who you are to him that simply doesn't include the possibility of romantic interaction. It might not be about you at all. Timing is important, but so are other uncontrollable factors. And clearly your situation is different in about a jillion ways (shorter time living together, not close beforehand, both single, etc.), but he sounds like an awesome respectul dude who is probably super careful about maintaining boundaries with his female friends, and that could certainly lead to a kind of blind spot about the possibility of dating/desiring you.

Despite all this, I'm totally crossing my fingers for you.
posted by dizziest at 12:30 PM on August 13, 2012

Hi There - I'm so sorry it took me so long to update you folks on what's happened - I only just mustered up the courage to say something to him yesterday... I was too nervous, this whole time, to say something in person so I finally got so frustrated with myself that I caved in and wrote him an e-mail... He read it, yesterday before he went to work and we haven't seen each other since, and I haven't heard back from him yet so I can only hope he's thinking about it! I'll let you know what happens!
posted by bzzt at 8:09 AM on October 3, 2012

You did the right thing. I'll be honest: I think that at this point it's most likely to achieve only some release from thinking about this and remove any long-term regret that you never mentioned it. But that's pretty huge. Count mastering your nervousness as a success as well. Mustering up this kind of courage is a very useful and widely applicable habit to acquire.

Anyway, you never know--good luck!
posted by Monsieur Caution at 11:02 PM on October 3, 2012

Hi Everyone - My room mate read the e-mail on Tuesday and when I got home from work yesterday he talked to me and told me he liked me too (romatically) and wants to start dating!! :D I am thrilled, of course! We're going to go on an honest-to-goodness date and take it slow, but it is such a relief to know he was thinking the same things about me! Thank you all so much for your advice - I really like this guy and I am going to do my best to make it work!
posted by bzzt at 12:29 PM on October 4, 2012 [12 favorites]

YAY! So so happy for you! I checked this thread daily to see if there were any updates! I was nervous and excited for you and so happy with the outcome!
Congratulations on having the courage :)
Good luck!
posted by MsOz at 8:48 PM on October 4, 2012 [1 favorite]

I'm so pleased to hear this, bzzt! What good news! :-) Mazel Tov!
posted by UniversityNomad at 9:02 AM on October 11, 2012 [1 favorite]